IL39719A - N-arylcarbamic acid esters,their preparation and their use as plant-growth regulators - Google Patents
N-arylcarbamic acid esters,their preparation and their use as plant-growth regulatorsInfo
- Publication number
- IL39719A IL39719A IL7239719A IL3971972A IL39719A IL 39719 A IL39719 A IL 39719A IL 7239719 A IL7239719 A IL 7239719A IL 3971972 A IL3971972 A IL 3971972A IL 39719 A IL39719 A IL 39719A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- carbon atoms
- alkyl
- process according
- formula
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims 9
- 150000002148 esters Chemical class 0.000 title claims 6
- 239000005648 plant growth regulator Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 35
- 238000000034 method Methods 0.000 claims 24
- 125000004432 carbon atom Chemical group C* 0.000 claims 21
- 125000000217 alkyl group Chemical group 0.000 claims 20
- 125000001188 haloalkyl group Chemical group 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- -1 aralkyl radical Chemical class 0.000 claims 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- 239000003085 diluting agent Substances 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 239000011230 binding agent Substances 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 150000003254 radicals Chemical class 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 239000005864 Sulphur Substances 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000005354 acylalkyl group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 150000001768 cations Chemical class 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000005131 dialkylammonium group Chemical group 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 230000001105 regulatory effect Effects 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000005208 trialkylammonium group Chemical group 0.000 claims 2
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 claims 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims 1
- 150000005840 aryl radicals Chemical class 0.000 claims 1
- 229910001424 calcium ion Inorganic materials 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 230000012010 growth Effects 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 229910001425 magnesium ion Inorganic materials 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 150000007530 organic bases Chemical group 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 230000008635 plant growth Effects 0.000 claims 1
- 239000003495 polar organic solvent Substances 0.000 claims 1
- 229910001414 potassium ion Inorganic materials 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 229910001415 sodium ion Inorganic materials 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/20—N-Aryl derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Furan Compounds (AREA)
Claims (46)
1. N-arylcarbamic acid esters of the general formula .in which - - . - _. -- —- - R is alkyl,. alkynyl or haloalkyl, R1, R2 and R3, which may be identical or different, are each .' ^ hydrogen, alkyl, alkpxy:..or halogen, R. is alkyl, alkenyl, alkynyl, haloalkyl or optionally halo-'.' • gen substituted, phenyl, or is the grouping ■■' 1 R5-C- \ ·" ■ .· ■ " " '' ■ ' · · '· ' {' . wherein , ! R5 is hydrogen, alkyl, alkenyl, cycloalkyl, oycloalkenyl, halo- · '.' , alkyl, acylalkyl, alkoxycarbonylalky'l, an aryl radical optionally being substituted by alkyl, haloalkyl, alkoxy and/or halogen; an aralkyl or an aryloxyalkyl, the aryl part of the . two last-mentioned radicals optionally carrying one or more substituents selected from halogen, ' alkyl, haloalkyl or alkoxy, and the alkyl part of the aralkyl radical' optionally . being substituted by one or more halogen atoms; or R^ is 'the grouping - and Y and Υ· are oxygen or sulphur.
2. Compounds* according to Claim 1 in which R is straight- ' ' t chain or branched alkyl with 1 to 4 carbon efcoms, straight-chain or branched alkynyl with 3 to 6 carbon atoms or haloalkyl with 1 to.4 carbon atoms and 1 to 3 halogen atoms; R ,. R and ^ are each hydrogen, fluorine, chlorine, bromine, alkyl with 1 to carbon atoms or straight-chain or branbhed alkoxy with 1 to 4 carbon atoms; and R^ is straight-chain or branched alkyl with I tp' 6 carbon atoms or haloalkyl with 1 to 6 carbon atoms an 1 to 3 halogen atoms, straight-chain or branched alkenyl ' . •with 3 to 6 carbon atoms, straight-chain or branched alkynyl ;!■ with 3 to £ carbon atoms or phenyl optionally substituted 5 by one or more chlorine atoms, or is the grouping R -C=Y-' - wherein Y' is oxygen or sulphur and ^ is hydrogen, straight- chain or branched alkyl with 1 to 18 carbon atoms, straight- . chain or branched alkenyl, with 3 to 12 carbon atoms, cyclo- - alkyl with 3 to 8 carbon atoms,, cycloalkenyl with 5 to 8 carbon .atoms, haloalkyl with 1 to 6 carbon atoms and 1 to- 5 halogen atoms, acylalkyl with 1 to 4 carbon atoms in the acyl part and 1 to 4 carbon atoms in the alkyl part, alkoxycarbonyl- ... alkyl with 1 to 4 carbon atoms in the alkoxy part and 1 to '· ·' 4 carbon atoms in the alkyl part, aryl with 6 to 10 carbon' atoms optionally being substituted by one or more radicals selected from halogen, straight-chain or branched alkyl or :· alkoxy with, in either case, 1 to 4 carbon atoms and haloalkyl with 1 or 2 carbon atoms and 1 to 5 halogen atoms, or an aralkyl or aryloxyalkyl radical with, in each case, ■6 to 10 carbon atoms in .the aryl moiety and A to 3. oarbon .· atoms in the alkyl moiety, the aryl part of. the two last-mentioned radicals optionally carrying one or more substituents * selected from fluorine', chlorine, bromine, straight-chain or branched alkyl or alkoxy with, in either case, 1 to 4 carbon : atoms and. haloalkyl with 1' or 2 carbon atoms and 1. to 5 halo- . gen atoms, and the alkyl part of the aralkyl radical optionally being substituted by one or more halogen atoms; or ^, is the grouping ..·*
3. « The compound of the formula )2
4. The compound of the formula )2
5. The compound of the formula
6. The compound of the formula
7. The compound of the formula
8. The compound of the formula
9. The compound of the formula
10. The compound of the formula
11. The compound of the formula
12. , The compound of the formula
13. The compound of the formula
14. · The compound of the formula
15. · The compounds hereinbefore mentioned in Tables 1 and 2.
16. The compounds hereinbefore mentioned in Tables 3 and 4·
17. A process for the preparation of an N-arylcarbamic acid ester according to any of claims 1 to 15 in which an N- chloromethyl-N^rylcarbamic acid ester of the general formula in which R, R^, R2 and R^ have the meanings stated in claim 1, is reacted (a) with a compound of the general formula H-Y-R4 (III) in which R and Y have the meanings stated in claim 1 , in the presence of an acid-hinding agent and optionally in the presence of a solvent or (b) with a compound of the general formula A-Y-R4 (IV) ·. in which R4 and Y have the meanings stated in claim 1 , and A represents a cation or a fraction of a cation, in the presence of a solvent.
18. A process according to claim 17(a) in which the reaction is effected in the presence of an inert organic solvent.
19. A process according to claim 17(a) or 18 in which the reaction is effected in the presence, as an acid-binding agent, of an alkali metal hydroxide, an alkali. metal carbonate or a tertiary organic base.
20. A process according to claim 19 in which the acid-binding agent is sodium carbonate, triethylamine or pyridine.
21. A process according to any of claims 17(a) and 18 to 20 in which the reaction is effected at from -20°C to +100°C.
22. A process according to claim 21 in which the reaction is effected at from - 10°0 to +80°C.
23. A process according to any of claims 17(a) and 18 to 22 in which 1 to 1.5 moles of the compound (III) and 1 to 2 moles of the acid-binding agent are used per mole of N-chloromethyl-N-arylcarbamic acid ester (II).
24. A process according to claims 17(b) in which A is an ammonium, alk lammonium, dialkylammonium ,trialkylammonium or alkali metal cation, or represents half of an alkaline earth metal cation.
25. A process according to claim 24 in which A is ammonium, dialkylammonium or trialkylammonium with 1 to 4 carbon atoms in each alkyl moiety, a sodium ion or a potassium ion, or represents half of a magnesium ion or of a calcium ion.
26. A process according to claim 17(b), 2 or 25 in which the reaction is effected in the presence of a polar organic solvent.
27. A process according to any of claims 17(b) and 24 to 26 in which the reaction is effected at from 0°C to 150°C.
28. A process according to claim 27 in which the reaction is effected at from 20°C to 100°C.
29. A process according to any of claims 17(b) and 2 to 28 in which the reactants (II) and (IV) are used in equimolar amounts.
30. A process according to any of claims: 17 to 29 in which the N-chloromethyl-N-arylcarbamic acid ester (II) is one that is hereinbefore specifically mentioned.
31. A process according to any of claims 17 to 30 in which the compound of the formula (III) or (IV) is one that is hereinbefore specifically mentioned.
32. A process for the preparation of a compound according to claim 1 substantially as hereinbefore described in any of Examples 1 to 4·
33. A process according to any of claims 17 to 29 adapted for the preparation of a compound according to claim 16.
34. Compounds, according to claim 1 whenever prepared by a process according to any of claims 17to 32.
35. Compounds according to claim 16 whenever prepared by a process according to any of claims 17 to 29.
36. A plant-growth-regulating caaposition containing as active ingredient a compound according to any of claims 1 to 15 and 34 in admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent.
37. A composition according to claim 36 containing from 0.1 to 95$ of the active compound, by weight.
38. A composition according to claim 37 containing from 0.5 to 90$ of the active compound, by weight.
39. A composition according to claim 36» 37 or 38 in which the active compound is according to claim 16 or 35.
40. A method of regulating the growth of plants which comprises, applying to the plants or a plant habitat a compound according to any of claims 1 to 15 and 34 alone or in the form of a composition containing as active ingredient a compound according to any of claims 1 to 15 and 34 in admixture with a diluent or carrier.
41. A method according to claim 40 in which the active compound is applied to an area of plant cultivatio in an amount of 0.1 to 25 kg per hectare.
42. A method according to claim 41 in which the active compound is applied to an area of plant cultivation in an amount of 0.5 to 20 kg per hectare.
43. A method according to claim 40, 41 or 42 in which the active compound is one that is hereinbefore mentioned in Example A or B.
44. A method according to claim 40, 41 or 42 in which the active compound is according to claim 16 or 35.
45. Plants of which the growth has been regulated by their being grown in areas in which immediately prior to and/or during the time of the growing a compound according to any of claims 1 to 15 and 34 was applied alone or in admixture with a diluent or carrier.
46. Plants according to claim 45 in which the active compound is according to claim 16 or 35»
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2131028A DE2131028B2 (en) | 1971-06-23 | 1971-06-23 | N-Aryl carbamic acid esters, process for their preparation and their use as plant growth regulators |
| DE19722214057 DE2214057A1 (en) | 1972-03-23 | 1972-03-23 | Substd n-aryl n-methyl carbamic acid esters - plant growth regulators |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL39719A0 IL39719A0 (en) | 1972-08-30 |
| IL39719A true IL39719A (en) | 1976-01-30 |
Family
ID=25761312
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL7239719A IL39719A (en) | 1971-06-23 | 1972-06-20 | N-arylcarbamic acid esters,their preparation and their use as plant-growth regulators |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3920727A (en) |
| JP (1) | JPS563342B1 (en) |
| AT (1) | AT317609B (en) |
| BE (1) | BE785264A (en) |
| CA (1) | CA1025458A (en) |
| CH (1) | CH584504A5 (en) |
| DD (2) | DD107910A5 (en) |
| DK (1) | DK131854C (en) |
| EG (1) | EG10699A (en) |
| FR (1) | FR2144302A5 (en) |
| GB (1) | GB1339116A (en) |
| HU (1) | HU165294B (en) |
| IL (1) | IL39719A (en) |
| IT (1) | IT960711B (en) |
| NL (1) | NL7208585A (en) |
| SE (1) | SE380519B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4230874A (en) * | 1976-09-13 | 1980-10-28 | Stauffer Chemical Company | N-(Benzenesulfonyl) carbamates-herbicidal antidotes |
| US4293701A (en) * | 1976-09-13 | 1981-10-06 | Stauffer Chemical Company | N-(Benzenesulfonyl) carbamates - herbicidal antidotes |
| DE2730325A1 (en) * | 1977-07-01 | 1979-01-11 | Schering Ag | CARBANILIC ACID-(3-UREIDO-PHENYL)- ESTER, PROCESS FOR THE PREPARATION OF THESE COMPOUNDS, AND HERBICIDES CONTAINING THEM |
| DE2732848A1 (en) * | 1977-07-18 | 1979-02-08 | Schering Ag | DIURETHANE, HERBICIDAL AGENTS CONTAINING THESE COMPOUNDS AND THE PROCESS FOR THEIR PRODUCTION |
| US4419523A (en) * | 1979-12-31 | 1983-12-06 | Stauffer Chemical Company | N-(Benzenesulfonyl) carbamates-herbicidal antidotes |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3547977A (en) * | 1967-10-27 | 1970-12-15 | Velsicol Chemical Corp | Novel carbanilates |
-
1972
- 1972-06-06 EG EG235/72A patent/EG10699A/en active
- 1972-06-20 DD DD171502*A patent/DD107910A5/xx unknown
- 1972-06-20 IL IL7239719A patent/IL39719A/en unknown
- 1972-06-21 IT IT26016/72A patent/IT960711B/en active
- 1972-06-21 DD DD163874A patent/DD100621A5/xx unknown
- 1972-06-21 CH CH929172A patent/CH584504A5/xx not_active IP Right Cessation
- 1972-06-21 SE SE7208183A patent/SE380519B/en unknown
- 1972-06-22 CA CA145,396A patent/CA1025458A/en not_active Expired
- 1972-06-22 HU HUBA2761A patent/HU165294B/hu unknown
- 1972-06-22 BE BE785264A patent/BE785264A/xx unknown
- 1972-06-22 DK DK312072A patent/DK131854C/en active
- 1972-06-22 NL NL7208585A patent/NL7208585A/xx not_active Application Discontinuation
- 1972-06-23 US US265909A patent/US3920727A/en not_active Expired - Lifetime
- 1972-06-23 FR FR7222914A patent/FR2144302A5/fr not_active Expired
- 1972-06-23 AT AT543172A patent/AT317609B/en not_active IP Right Cessation
- 1972-06-23 JP JP6250472A patent/JPS563342B1/ja active Pending
- 1972-06-23 GB GB2951772A patent/GB1339116A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK131854C (en) | 1976-02-16 |
| AT317609B (en) | 1974-09-10 |
| NL7208585A (en) | 1972-12-28 |
| EG10699A (en) | 1976-07-31 |
| IT960711B (en) | 1973-11-30 |
| DD107910A5 (en) | 1974-08-20 |
| DK131854B (en) | 1975-09-15 |
| SE380519B (en) | 1975-11-10 |
| US3920727A (en) | 1975-11-18 |
| CH584504A5 (en) | 1977-02-15 |
| CA1025458A (en) | 1978-01-31 |
| IL39719A0 (en) | 1972-08-30 |
| BE785264A (en) | 1972-12-22 |
| FR2144302A5 (en) | 1973-02-09 |
| GB1339116A (en) | 1973-11-28 |
| JPS563342B1 (en) | 1981-01-24 |
| HU165294B (en) | 1974-08-28 |
| DD100621A5 (en) | 1973-10-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU587710B2 (en) | A mold release composition, mixtures containing this mold release composition, a process for the production of molded articles and the molded articles obtained by this process | |
| IL39719A (en) | N-arylcarbamic acid esters,their preparation and their use as plant-growth regulators | |
| US4091037A (en) | Preparation of alkylthiomethylphenols | |
| GB840137A (en) | Thionophosphoric acid esters | |
| GB1447957A (en) | N-sulphenylated oxime-carbamates and their use as insecti cides acaricides and nematicides | |
| IL43299A (en) | Tetrasubstituted ureas,their preparation and their use as herbicides | |
| GB916704A (en) | Dithiophosphoric acid esters | |
| GB921558A (en) | Thiophosphonic acid esters | |
| GB847550A (en) | Phosphonic acid esters | |
| GB881977A (en) | Thiophosphonic acid esters | |
| GB969829A (en) | New phosphoric acid esters and process for their manufacture | |
| US3086047A (en) | Production of halogen substituted phosphines | |
| US3342871A (en) | Organic cyclophosphine sulfides and selenides and the preparation thereof | |
| US2602801A (en) | Method for the preparation of dialkyl beta-propiothetins | |
| GB834331A (en) | Thiophosphoric acid esters and their production | |
| GB808304A (en) | Thiophosphoric acid esters and their preparation | |
| GB1069078A (en) | Phosphorus compounds containing an arylsulphonic acid ester group and process for preparing them | |
| GB1451766A (en) | Process for the preparation of aromatic htiocarboxylic acid amides | |
| IL42212A (en) | 3,4-dihydro-4-oxo-quinazolinyl-phosphoric,thionophosphoric,-phosphonic and-thionophosphonic,acid esters and ester-amides,their production and their use as insecticides or acaricides | |
| US3955958A (en) | α-Cyano-α-dialkylphosphonato acetanilde herbicides | |
| GB1506092A (en) | Diphenyl ether amides and the use thereof as herbicides | |
| GB1501248A (en) | O-vinylthiono(thiol)phosphoric(phosphonic)acid esters process for their preparation and their use as insecticides | |
| GB1338356A (en) | Process for the preparation of n-unsubstituted-thio-phosphoric -phosphonic acid ester amides | |
| ES456925A1 (en) | N,n-dimethyl-o-(imidazol(5)yl)-carbamic acid esters process for their preparation and their use as arthropodicides | |
| GB1315227A (en) | S-alpha-alkoxycarbonylbenzyl-dithiophosphoric acid ester amides process for their preparation and their use as insecticides and acaricides |